N-(tert-butoxycarbonyl)glycine → N-[(1,1-Dimethylethoxy)carbonyl]glycine-4phenylmethoxy-2-butenyl ester

HRID 413402

반응식

HRID 413402 반응식
[CH3:1][C:2]([CH3:12])([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH3:3].[CH2:13]([O:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24]O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:14]1([CH2:13][O:20][CH2:21][CH:22]=[CH:23][CH2:24][O:10][C:9](=[O:11])[CH2:8][NH:7][C:5]([O:4][C:2]([CH3:12])([CH3:1])[CH3:3])=[O:6])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 11008492cis-4-Benzyloxy-2-buten-1-ol

생성물 1

HCID 69891095N-[(1,1-Dimethylethoxy)carbonyl]glycine-4phenylmethoxy-2-butenyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

N-[(1,1-Dimethylethoxy)carbonyl]glycine (21.9 grams, 0.125 mol), cis-4-benzyloxy-2-buten-1-ol (25 mL, 0.15 mol), and 4-dimethylaminopyridine (1.5 grams, 0.013 mol) are dissolved in methylene chloride and stirred at 0° C. Then N,N-dicyclohexylcarbodiimide (31 grams, 0.15 mol) in 30 mL methylene chloride is added and the reaction is stirred at 0° C. for five minutes. The reaction is then stirred for an additional twelve hours at 25° C. Additional methylene chloride is added and the reaction is washed consecutively with 1 N HCl, sodium bicarbonate and then with brine. The organic extract is dried over magnesium sulfate and the solvent evaporated in vacuo to give an orange oil which is absorbed onto silica gel and applied to a dry silica column. The column is eluted with hexane/EtOAc (9:1) then with hexane/EtOAc (8:2) Product fractions are combined and dried in vacuo to give the desired product.

후처리

  1. stirringthe reaction is stirred at 0° C. for five minutes
  2. stirringThe reaction is then stirred for an additional twelve hours at 25° C
  3. washthe reaction is washed consecutively with 1 N HCl, sodium bicarbonate
  4. extractionThe organic extract
  5. dry with materialis dried over magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customto give an orange oil which
  8. customis absorbed onto silica gel
  9. washThe column is eluted with hexane/EtOAc (9:1)
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-fc51b361b1384d3aa246311f51cb3677
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566381B1

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